The "Unconventional" Effect of Cysteine on the In Vitro Synthesis of Melanin.

Abstract

This report details some of our observations regarding the impact of cysteine on the air-mediated oxidation of catecholamines, particularly epinephrine. The intent was to synthesize light-colored, pheomelanin-like materials. Pheomelanin is commonly described as a material generated from a mixture of catecholamines and cysteine. However, we observed that (1) the presence of cysteine resulted in a concentration-dependent delay in the onset of color formation and (2) the presence of cysteine resulted in darker, more eumelanin-like materials. These effects were particularly impactful in the case of epinephrine. More elaborate studies involving other amino acids or scaled-up reactions were conducted with epinephrine as the precursor. These studies show that other amino acids, e.g., methionine or serine, could lead to darker materials, but none were as impactful as cysteine. Although our results are in contrast to typical descriptions regarding the impact of cysteine on the synthesis of melanin, they may reflect crucial differences between the in vitrovsin vivo synthesis of pheomelanin.